Mevalonic acid

Base Information

• Chemical Name: Mevalonic acid
• CAS No.: 17817-88-8
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• DSSTox Substance ID: DTXSID801314151
• Nikkaji Number: J385.671B
• Wikipedia: Mevalonic_acid
• Wikidata: Q241678
• Metabolomics Workbench ID: 1480
• ChEMBL ID: CHEMBL1794734
• Mol file: 17817-88-8.mol

Synonyms:Acid, Mevalonic;Mevalonate;Mevalonic Acid

Chemical Property of Mevalonic acid

Chemical Property:

• PSA: 77.76000
• LogP: -0.40550
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

R-MevalonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCO)(CC(=O)O)O
• Isomeric SMILES: C[C@@](CCO)(CC(=O)O)O
• Recent ClinicalTrials: Safety Study of MVA Smallpox Vaccine in Subjects With a History of Atopic Dermatitis (AD)
• Uses: R-Mevalonic Acid, can stimulate leukemic cells from some patients with B cell chronic lymphocytic leukemia (CLL) to enter the cell cycle in vitro and to synthesize DNA.

Technology Process of Mevalonic acid

There total 13 articles about Mevalonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

mevalonolactone (674-26-0,503-48-0) → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With water; potassium hydroxide; at 40 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.11.040 DOI:10.1016/j.ejmech.2014.11.040

Reference yield:

→ D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01566a080

Reference yield:

3-Hydroxy-3-methyl-6,6-diphenyl-hex-5-enoic acid ethyl ester → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol / Ambient temperature

2: (i) O₃, CH₂Cl₂, MeOH, (ii) NaBH₄, H₂O

With sodium hydroxide; In methanol;

upstream raw materials:

D,L-mevalonic acid

(R)-mevalonolactone

mevalonolactone

meglutol

Downstream raw materials:

elymoclavine

2-methyl-but-2-ene

2-Methyl-1-butene

3-Methyl-1-butene

Refernces

• 1、 Saravanan, Thangavelu,Junker, Sebastian,Kickstein, Michael,Hein, Sascha,Link, Marie-Kristin,Ranglack, Jan,Witt, Samantha,Lorillière, Marion,Hecquet, Laurence,Fessner, Wolf-Dieter. "Donor Promiscuity of a Thermostable Transketolase by Directed Evolution: Efficient Complementation of 1-Deoxy-d-xylulose-5-phosphate Synthase Activity". supporting information. p. 5358 - 5362. Retrieved 2017/04/27.
• 2、 -. "Process For The Production Of Isoprenol From Mevalonate Employing a Diphosphomevalonate Decarboxylae". Paragraph 0103. . Retrieved 2016/03/04.